US4349677A - 3,4-Dihydro-3,4-isoquinolinedione 4-oxime - Google Patents

3,4-Dihydro-3,4-isoquinolinedione 4-oxime Download PDF

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Publication number
US4349677A
US4349677A US06/319,443 US31944381A US4349677A US 4349677 A US4349677 A US 4349677A US 31944381 A US31944381 A US 31944381A US 4349677 A US4349677 A US 4349677A
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United States
Prior art keywords
isoquinolinedione
oxime
dihydro
compound
water
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US06/319,443
Inventor
Thomas J. Schwan
Homer A. Burch
Joseph E. Gray
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ATK Launch Systems LLC
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Morton Norwich Products Inc
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Priority to US06/319,443 priority Critical patent/US4349677A/en
Assigned to MORTON-NORWICH PRODUCTS, INC. reassignment MORTON-NORWICH PRODUCTS, INC. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BURCH, HOMER A., GRAY, JOSEPH E., SCHWAN, THOMAS J.
Application granted granted Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms

Definitions

  • This invention is concerned with chemical compounds.
  • it is concerned with the compound 3,4-dihydro-3,4-isoquinolinedione 4-oxime.
  • This compound is useful as an antifungal agent.
  • a peroral dose of about 35 mg/kg to 50 infected mice a reduction in viable cell count is observed in both spleen and heart organs.
  • Suitable compositions for convenient use of the compound of this invention consist of conventional dosage forms such as solutions, tablets, suspensions and capsules using commonly employed excipients and adjuvants of the pharmaceutical art with which there is no incompatibility.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The compound 3,4-dihydro-3,4-isoquinolinedione 4-oxime is useful as an antifungal agent.

Description

This invention is concerned with chemical compounds. In particular, it is concerned with the compound 3,4-dihydro-3,4-isoquinolinedione 4-oxime.
This compound is useful as an antifungal agent. For example, when administered perorally by gavage in water to mice systemically infected with Torulopsis glabrata, salutary effect is elicited. In a peroral dose of about 35 mg/kg to 50 infected mice a reduction in viable cell count is observed in both spleen and heart organs. Suitable compositions for convenient use of the compound of this invention consist of conventional dosage forms such as solutions, tablets, suspensions and capsules using commonly employed excipients and adjuvants of the pharmaceutical art with which there is no incompatibility.
In order that this invention may be readily available to and understood by those skilled in the art the following now preferred method of making it is set forth:
To a solution of 47.1 g (0.48 mole) of conc. H2 SO4 in 390 ml of water stirred at 30° was added quickly 17.3 g (0.12 mole) of 3-aminoisoquinoline. The solution was cooled to 5° and a solution of 24.8 g (0.36 mole) of sodium nitrite in 60 ml of water was added over 45 min at 5°-10°. The mixture was stirred at 3°-7° for 2.5 hr and the solid was filtered, washed with 2×75 ml of H2 O, and dried at 60° to give 20.2 g (88%) of the product. Recrystallization from water gave an analytical sample, m.p. 190°-200° (dec.).
Anal. Calcd. For C9 H6 N2 O2.H2 O: C, 56.25; H, 4.19; N, 14.58; H2 O, 9.37. Found: C, 56.02; H, 4.25; N, 14.44; H2 O, 10.1.

Claims (1)

What is claimed is:
1. The compound 3,4-dihydro-3,4-isoquinolinedione 4-oxime.
US06/319,443 1981-11-09 1981-11-09 3,4-Dihydro-3,4-isoquinolinedione 4-oxime Expired - Lifetime US4349677A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US06/319,443 US4349677A (en) 1981-11-09 1981-11-09 3,4-Dihydro-3,4-isoquinolinedione 4-oxime

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/319,443 US4349677A (en) 1981-11-09 1981-11-09 3,4-Dihydro-3,4-isoquinolinedione 4-oxime

Publications (1)

Publication Number Publication Date
US4349677A true US4349677A (en) 1982-09-14

Family

ID=23242258

Family Applications (1)

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US06/319,443 Expired - Lifetime US4349677A (en) 1981-11-09 1981-11-09 3,4-Dihydro-3,4-isoquinolinedione 4-oxime

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4150135A (en) * 1974-09-09 1979-04-17 E. I. Du Pont De Nemours And Company Substituted 4a-phenyl-N-phenylalkyl-cis-decahydroisoquinolines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4150135A (en) * 1974-09-09 1979-04-17 E. I. Du Pont De Nemours And Company Substituted 4a-phenyl-N-phenylalkyl-cis-decahydroisoquinolines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Buu-Hoi, et al., "J. Het. Chem." vol. 5 (8), 1968, pp. 545-547. *

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